Ep. 385 How to design a portfolio career that actually works for you

Estimated reading time: 15 minutes

Forty percent of professionals under 35 now earn from multiple income streams – and yet most people who end up with a portfolio career stumble into it by accident rather than by design. Anna Lundberg explores what a portfolio career really is, why it’s rising so fast, and how to build one with the intentional architecture it needs to be both sustainable and fulfilling.

Key moments

[00:00] Introduction – What this episode is for and who it’s designed to help

[01:06] Anna’s own story – From being good at everything to finding a name for it

[04:51] Defining a portfolio career – What it actually means and what it looks like in practice

[05:24] The numbers – Why portfolio careers are no longer a niche lifestyle choice

[05:45] Pull and push factors – Why more people are moving this way

[06:39] Cultural shift – The single-employer model losing its grip

[07:25] The real challenges – Context switching, admin overhead, and the burnout trap

[09:43] Portfolio vs. multiple jobs – Why intentional design makes all the difference

[10:56] A framework for structuring your portfolio – Anchor, growth, and passion layers

[13:30] How to audit and tidy what you already have – Practical steps to bring order to the mix

Key resources

• Emily Wapnick’s TEDx talk: Why some of us don’t have one true calling
• Squiggly Careers podcast by Amazing If (Helen Tupper and Sarah Ellis)
• Anna Lundberg’s book: Leaving the Corporate 9 to 5 – includes a full section on portfolio careers
• Book a free call with Anna: onestepoutside.com/call

Portfolio career design

Okay, so if you search Anna Lundberg portfolio career, which I just did, AI tells you that Anna Lundberg has a portfolio career. So I was actually looking for an article I wrote a long time ago, 10 years ago, in fact, I think it was. But yes, interestingly and amusingly, after 10 years plus of building this way, it’s really great to actually see that it’s finally been recognised as a real thing. And AI, Google, Gemini, whatever it is who answered me, recognising that that is what I do. And so that’s what we’re doing today. We’re going to go deep on what a portfolio career actually is, why it’s rising so fast, and how to design one that works rather than just kind of surviving a random stack of commitments, which let’s face it, can just become hugely complex and overwhelming.

So my story, I suppose – I wrote about this in 2016. And at the time, I guess it was quite a niche concept. I don’t know. It’s certainly been quiet for a few years. And now suddenly people are sprouting up and talking about it. There’s some amazing people. Anna Mack, who I think is based in Australia, has got an amazing portfolio career operating system concept she’s doing down there. I’ve seen more and more people. We’ve talked about generalists. I had Julie on many months ago and I was on her podcast, in fact, and we talked about portfolio career and generalists. Another one of my articles that was a more successful article over the years was in fact exactly that, the curse of the generalist. And so these concepts are all kind of intertwined – and being multi-passionate, multi-potentialite, as Emily Wapnick called it back in the day. She had a very pioneering TED talk on, I think, something like why it’s okay not to have one calling or something like that and built a whole world around that as well.

I guess my own experience of this was – and this is a bit of a humble brag – but at school I was kind of good at everything and interested in everything and I never had this one thing. I met a girl when I first moved to Geneva, Switzerland, and she had always wanted to be a dancer and that was her thing and she ended up kind of living in a squat and, you know, she cared so much that she wasn’t focused all about money, for example. And there were others who are like, no, I really want to go make millions here or go into finance or whatever it is, politics, right? I did the International Baccalaureate instead of A-levels, which actually helped me keep my options open because the IB, you do six subjects plus some other stuff, kind of philosophical things and all sorts. Similarly, I’m embarrassed to say at university, I did philosophy, politics and economics because it gave me the breadth. I continued then to do a master’s. I am an ENTP, if you’re familiar with Myers-Briggs, which again is very versatile, broad array of interests, difficult to zero in on one thing. I’m also a Libra, if we’re going to count astrology, which is sort of being indecisive – that doesn’t really help.

So the dark side of all this is that it can look quite confused, unfocused, uncommitted, right? And internally, it can feel like imposter syndrome, because you’re always dabbling rather than going deep in one lane. And I certainly had that with sports, for example, I enjoyed all the sports. So I was never good at anything. Musical instruments, I did like grade one piano, grade five clarinet. You know, I play ukulele now a little bit. I wanted to learn guitar, et cetera, et cetera. Right. So you can hear and maybe recognise yourself in this as well.

Marketing similarly, in fact, was quite a clever accidental fit because it was both creative and technical. And especially when I specialised in digital, I got to sit between kind of the more creative marketing side and the more techie side. And that really, really suited me. I got to wear lots of different hats. And obviously now working for myself, I have even more hats and even more range. So I think what’s important and what we realise as generalists, multi-potentialites, whatever we want to call ourselves with a portfolio career, is that what looks like an inability to commit is in fact the earliest version of a portfolio career in the making. We just didn’t have a name for it.

So I suppose a simple definition is building your professional life from multiple income streams instead of a single full-time job. So if you can imagine a few concrete examples just so you can visualise it if you are new to the concept – let’s say a fractional CMO plus two non-exec director roles, coaching plus facilitation plus writing plus a part-time employed role maybe even, consulting and speaking plus maybe you are on a small online community, or a part-time job plus a side business plus a board seat, right?

There’s a 2024 survey I found that said over 40% of professionals under 35 earned from multiple jobs. UK Department for Education research says that 63% of adults either already have multiple roles or plan to, and portfolio careers are up 37% since pre-pandemic. So this is no longer a niche lifestyle choice. It’s really the direction of travel.

And let’s look at then why it’s rising. I think there’s, as ever, pull factors and push factors, and there’s a bigger cultural shift. So in terms of the pull factors, we actively want flexibility, variety, autonomy, more than we want a single employer identity. So in one UK study, 22% cited wanting something different and 70% wanting to retrain as drivers. And tech and remote work, of course, have made it practically viable in a way it wasn’t before. So I think that’s the pull side of things.

Then on the push side – post layoffs, burnout, restructuring. A lot of us, I think, start a portfolio by accident. You know, you lose a job, you pick up a contract, you add something else, and then you realise you can intentionally upgrade the patchwork into more of a coherent, intentional design. So those are the push factors. And then a bit more broadly, I suppose, there is a cultural shift. The single ladder – I really love the squiggly careers concept, I’ve talked about before, Helen Tupper, Sarah Ellis. And the single ladder, the single employer, single identity model is losing its grip. The success scripts are really being rewritten. And, you know, this connects directly back to last week’s episode and the one before that when I was talking about women opting out and that whole conversation, right? Because what we’re actually opting into often ends up being more of a portfolio because it gives us more variety, flexibility, and fulfilment.

Okay, so I guess the challenges of having a portfolio, before I even go into more about it, I suppose, is that it can be genuinely hard. And this is very much speaking from personal experience because context switching is cognitively expensive, right? You’re moving between different client worlds, different problems, different relationships. And that takes more out of you than just staying in one lane and always delivering the same thing. On the other hand, of course, it keeps it interesting, right? So that’s the pros and cons. Admin overhead can be quite heavy with multiple contracts, multiple invoices, multiple relationships to maintain.

Let’s be honest, even with multiple streams, you can still have lumpy months. It can still be a bit of a feast or famine roller coaster. As ever, we don’t get benefits and employer pension contributions, sick pay, etc. unless part of that portfolio is a more stable actual employment. And you can potentially feel a bit isolated. I suppose, you know, like my playing lots of sports – I never became like a skier or a surfer, you know, I don’t have that one identity, always a bit of an imposter in each of those, and you don’t really belong anywhere. So you can potentially feel a bit isolated. The good news is that there are so many of us with portfolio careers, so we can identify with each other that way too. But it can be very hard, right? I just want to be honest about that.

There is also the burnout trap, which to be honest is always looming large, because people assume that portfolio means more freedom, but it can also mean more chaos, right? If you’re simply stacking roles without dropping anything, adding more, more, more, then you’re not making space. You’re just creating a really heavy multiple job scenario for you. So you ask – okay, what do I need to stop doing to make space for this other thing? And then thinking about your energy, I suppose – how much can you realistically hold within your actual life? Because again, if you’ve only got four or five hours every day, then that maths becomes really useful. You’ve got a fixed number of hours, and a portfolio career doesn’t create more of them. It actually requires more different things – business development in multiple areas, marketing on multiple channels, potentially. So you need to really think carefully about how you’re using your time effectively, depending on what your immediate priority is – if it’s money right away, or if it’s balance, or what the biggest need for you is.

So a portfolio career is not having three jobs because your employer underpays you. That’s kind of an economic necessity, really, rather than intentional design. A genuine portfolio career has to be a deliberate choice with deliberate architecture. But let’s look at the positives. Why is now a good time? Well, the economic case has strengthened, I’d say, recently. Fractional executive demand is up 46% year on year in 2024. Companies are definitely increasingly willing to pay for expertise in slices rather than full-time headcount. Ironically, when redundancies are made, there are actually more opportunities for you as an independent expert to come in. And the gig economy has matured – there’s so much more infrastructure, more acceptance of it as a valid career choice and more tools available. But I should distinguish between what I’m talking about here and the gig economy in its worst form – you know, zero hours contracts, delivery-type platform dependency – because a portfolio career is really an expert deliberately diversifying. It’s not a worker who’s being casualised by someone else’s business model, and that is really important in terms of our agency and positioning.

So if you don’t want it to become just multiple full-time jobs, which is not going to be a solution for anyone, it’s really important to consider what’s your big message, what’s your coherent umbrella. So in my case, redefining success, redefining how we work and lead, and then that can be translated into working inside companies, and it can be translated into supporting people outside companies, right? So it needs to at least make sense to you. And the more it makes sense, the easier it’ll be to have a coherent LinkedIn profile, to be able to speak cohesively and confidently at a networking event or anything like that.

And you might also consider having different parts of your work serving a different purpose. So you can have kind of an anchor – that’s your main reliable income stream. Probably that’s going to be more like consulting, a fractional role, stable part-time employment. It pays the bills, it gives you a foundation to build from, and you kind of need that to be working before you add layers on, right? Then maybe you would look at where you want to be in a few years’ time. Okay, this is more visibility and future income. So a podcast, book, developing IP, strategic advisory – they may not pay well now, but they’re going to be the source of growth and take you in the direction that you want to go in the future. You know, publishing a book is not like, ta-da, now you’ve made it and the money will flow in. But having that is a massive credibility piece and a huge play for future work, right?

And then possibly there’s a passion impact layer – maybe more creative work that you want to do, or volunteering, being on a non-profit board, mentoring, or some early experiments. It’s not going to be the dominant stream for you, but it feeds you in a way that maybe your most reliable income stream doesn’t from a creative perspective, right? And it’s really important to make this sustainable and enjoyable, but it can’t dominate because it’s not necessarily bringing in the income.

So really, I’m all about intentional business design, and especially with this kind of portfolio it has to be designed, not just haphazardly accumulated. Because again, if you end up with a random stack of commitments and you’re not intentionally choosing what’s there, if you’re just saying yes to everything, then that can become pretty unsustainable in the long term.

A few final thoughts in terms of how to start, or how to tidy up your portfolio with that in mind. First is auditing what you already have – if you’ve already got different income streams and commitments, try to label them. Is this an anchor bringing income stability? Is this the future growth piece? Or is this a passion layer that needs to be there, but isn’t going to dominate immediately because it doesn’t yet bring in the income? And be really honest about which is which – anchor, growth, or passion. Some things people call growth may just be passion, right? And it’s not bringing in income, for example. It’s just important to be clear.

Then decide what to drop. This is so important because a portfolio can only work within a humane number of hours. So what needs to go or shrink to make space for what you’re adding? It’s so easy to add things on, so order what you have and decide what to drop.

And then a big piece of this – it’s really a shift in your identity. It’s not I have a job. It’s I have a portfolio career. I am the CEO of this portfolio. I know it sounds fluffy, but it really shifts how you introduce yourself. Not like, oh, I did a bit of coaching, I did a bit of this. No – I am an expert in this, I do a few different things, I have this book and I do speaking and whatever. So it’s how you introduce yourself, it’s how you structure your week to support that portfolio model, and how you make decisions. All of that changes when you stop seeing yourself as someone who’s just dabbling and experimenting, versus no, this is a container that I’m designing deliberately.

So you can consider having theme days to reduce context switching, separate finances for different streams if the volume justifies it and if that helps, and really clear contracts and scope on different engagements. I think portfolio careers especially can live or die on boundaries.

This is personally very relevant to me – that article from 10 years ago, my Myers-Briggs profile, and that feeling of always being pulled in different directions. But I want us to see this as a strength. It’s just a different operating system, right? In fact, it’s not better or worse than being a specialist, it’s just different, and it suits some of us more than others. And it turns out there is a growing infrastructure for people who build this way – communities, frameworks, tools, role models. I mentioned Emily Wapnick’s TEDx talk on why some of us don’t have one true calling, which is great to watch if you’re new to this idea. And my first book, Leaving the Corporate 9 to 5, introduced different alternatives to the corporate 9 to 5, including a whole section on portfolio careers.

So the question is not what’s wrong with me? Why can’t I pick just one thing? It’s how do I design a portfolio that plays to how I actually work? If you are trying to figure that out, I’d love to hear from you. You can always book a free call at onestepoutside.com/call – just have a chat about how you’re thinking, whether you’re starting out or whether you’re further along and you’re just wanting to bring an extra layer of intentional design to what you’re working on. I hope that more and more of us are seeing the light when it comes to this portfolio way of working, and it can only be a good thing that we’re finding ways to work that give us the freedom and flexibility as well as doing more fulfilling work in a way that works for us. Thanks so much – I’ll see you next week. Bye for now.